Substituted oximes

ABSTRACT

The invention relates to novel substituted oximes, to a process for their preparation and to their use as fungicides.

FIELD OF THE INVENTION

The invention relates to novel substituted oximes, to a process fortheir preparation and to their use as fungicides.

BACKGROUND OF THE INVENTION

It is already known that certain compounds of a similar constitution tothose described below have fungicidal properties (compare, for example,EP-A 525516). However, the fungicidal action of these compounds is, inparticular at low application rates, not entirely satisfactory.

SUMMARY OF THE INVENTION

Substituted oximes according to the invention have microbicidalactivity.

DETAILED DESCRIPTION

This invention, accordingly, provides the novel substituted oximes ofthe general formula (I),

in which

E represents methoxy, ethoxy, amino or methylamino,

G represents a grouping

 in which

R¹ and R² are identical or different and independently of one anothereach represents optionally substituted alkyl, alkenyl, alkinyl, aryl,cycloalkyl, alkylcarbonyl or arylcarbonyl, or

R¹ and R² together with the nitrogen atom to which they are attachedform a saturated or unsaturated heterocyclic ring, and

Z represents cyano, alkoxycarbonyl, alkoxy, alkylthio, alkylsulfonyl,cycloalkoxy or in each case optionally substituted alkyl, cycloalkyl,cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,

R represents hydrogen, alkyl or in each case optionally substitutedcycloalkyl or aryl, and

L¹, L², L³ and L⁴ are identical or different and independently of oneanother each represents hydrogen, halogen, cyano, nitro, in each caseoptionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulfinylor alkylsulfonyl.

In the definitions, the saturated or unsaturated hydrocarbon chains,such as alkyl, are in each case straight-chain or branched, including incombination with heteroatoms, such as in alkoxy or alkylthio.

Halogenoalkyl is partially or fully halogenated alkyl. In the case ofpolyhalogenated halogenoalkyl, the halogen atoms can be identical ordifferent. Preferred halogen atoms are fluorine and chlorine and inparticular fluorine. If the halogenoalkyl carries further substituents,the maximum possible number of halogen atoms is reduced to the remainingfree valencies.

Halogen generally represents fluorine, chlorine, bromine or iodine,preferably fluorine, chlorine or bromine, in particular fluorine orchlorine.

Heterocyclyl represents saturated or unsaturated, and also aromatic,cyclic compounds in which at least one ring member is a heteroatom, i.e.an atom different from carbon. If the ring contains a plurality ofheteroatoms, these can be identical or different. Preferred heteroatomsare oxygen, nitrogen and sulfur. If the ring contains a plurality ofoxygen atoms, these are not adjacent. If appropriate, the cycliccompounds form, together with other carbocyclic or heterocyclic,fused-on or bridged rings, a polycyclic ring system. A polycyclic ringsystem can be attached via the heterocyclic ring or a fused-oncarbocyclic ring. Preference is given to mono- or bicyclic ring systems,in particular to mono- or bicyclic aromatic ring systems.

Benzoheterocyclyl, as a sub-group of heterocyclyl, representsheterocyclyl to which a phenyl ring is fused.

Dibenzoheterocyclyl represents heterocyclyl to which two phenyl ringsare fused.

Furthermore, it has been found that the novel substituted oximes of thegeneral formula (I) are obtained when oximes of the formula (II)

in which

G, R and Z are as defined above,

are reacted with a halogen compound of the general formula (III)

in which

E, L¹, L², L³ and L⁴ are as defined above and

X represents halogen,

if appropriate in the presence of a diluent and if appropriate in thepresence of a catalyst.

Compounds of the formula (I) in which E represents amino or methylaminocan also be obtained in a simple manner from compounds of the formula(I) in which E represents methoxy or ethoxy, by reaction with ammoniaand methylamine, respectively, if appropriate in the presence of adiluent (compare also Tetrahedron Letters 1993, 5151-5154).

Compounds of the formula (I) in which R represents alkylsulfonyl canalso be obtained in a simple manner from compounds of the formula (I) inwhich R represents alkylthio, by generally known oxidation methods.

Compounds of the formula (I) in which R represents alkoxy can also beobtained in a simple manner from compounds of the formula (I) in which Rrepresents alkylsulfonyl, by generally known substitution reaction withalcohols.

Finally, it has been found that the novel substituted oximes of thegeneral formula (I) have highly potent fungicidal action.

If appropriate, the compounds according to the invention can be presentas mixtures of different possible isomeric forms, in particular ofstereoisomers, such as, for example, E and Z or optical isomers. What isclaimed are both the E and the Z isomers, the individual enantiomers,the racemates, and any mixtures of these isomers.

Preference is given to substituted oximes of the formula (I) in which

E represents methoxy, ethoxy, amino or methylamino,

G represents a grouping

 in which

R¹ and R² are identical or different and independently of one anothereach represents alkyl or alkylcarbonyl having 1 to 6 carbon atoms,alkenyl having 2 to 6 carbon atoms or alkinyl having 2 to 6 carbonatoms, each of which is optionally substituted by halogen or alkoxyhaving 1 to 4 carbon atoms, or represents cycloalkyl having 3 to 8carbon atoms, which is optionally substituted by halogen, alkyl oralkoxy having in each case 1 to 4 carbon atoms, or represents phenyl,phenylalkyl or heterocyclylalkyl having 1 to 4 carbon atoms in the alkylmoiety or phenylcarbonyl, each of which is optionally substituted in thephenyl moiety or heterocyclyl moiety, the substituents being selectedfrom the list below:

halogen, cyano, nitro, alkyl, alkoxy, alkylthio, alkylsulfinyl oralkylsulfonyl having in each case 1 to 6 carbon atoms, halogenoalkyl,halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl orhalogenoalkylsulfonyl having in each case 1 to 6 carbon atoms and 1 to13 identical or different halogen atoms, in each case halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11identical or different halogen atoms, or

R¹ and R² together with the nitrogen atom to which they are attachedform a saturated or unsaturated heterocyclic ring having 5 or 6 ringmembers,

R represents alkyl having 1 to 4 carbon atoms or represents cycloalkylhaving 3 to 6 carbon atoms or phenyl, each of which is optionally mono-to tetrasubstituted by halogen or alkyl, preferably represents methyl orcyclopropyl, in particular methyl,

Z represents cyano, alkoxycarbonyl, alkoxy, alkylthio or alkylsulfonylhaving in each case 1 to 4 carbon atoms in the alkyl moiety, cycloalkoxyhaving 5 or 6 carbon atoms or

represents alkyl or halogenoalkyl having in each case 1 to 4 carbonatoms and being in each case optionally monosubstituted by cyano oralkoxy, or

represents cycloalkyl or cycloalkylalkyl having in each case 3 to 7carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in thealkyl moiety, each of which is optionally mono- to tetrasubstituted byhalogen or alkyl; or

represents heterocyclyl, benzoheterocyclyl, dibenzoheterocyclyl orheterocyclylalkyl having in each case 3 to 7 ring members in theheterocyclyl moiety and 1 to 4 carbon atoms in the alkyl moiety andbeing optionally substituted by halogen, alkyl, alkoxy, alkylthio,alkylsulfinyl or alkylsulfonyl having 1 to 4 carbon atoms,halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl orhalogenoalkylsulfonyl having 1 to 4 carbon atoms and 1 to 9 halogenatoms or phenyl;

or represents aryl or arylalkyl having in each case 6 to 10 carbon atomsin the aryl moiety and 1 to 4 carbon atoms in the alkyl moiety and beingin each case optionally mono- to tetrasubstituted in the aryl moiety byidentical or different substituents, the possible substituentspreferably being selected from the list below:

halogen, cyano, nitro, amino, carbamoyl, thiocarbamoyl;

in each case straight-chain or branched alkyl, alkoxy, alkoxyalkyl,alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylthio,alkylsulfinyl or alkylsulfonyl having in each case 1 to 8 carbon atoms;

in each case straight-chain or branched alkenyl or alkenyloxy having ineach case 2 to 6 carbon atoms;

in each case straight-chain or branched halogenoalkyl, halogenoalkoxy,halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl havingin each case 1 to 6 carbon atoms and 1 to 13 identical or differenthalogen atoms;

in each case straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11identical or different halogen atoms;

in each case straight-chain or branched alkylamino, dialkylamino,alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl orarylalkylaminocarbonyl having 1 to 6 carbon atoms in the respectivehydrocarbon chains;

cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms;

in each case doubly attached alkylene having 3 or 4 carbon atoms,oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2carbon atoms, each of which is optionally mono- to tetrasubstituted byidentical or different substituents from the group consisting offluorine, chlorine, methyl, trifluoromethyl and ethyl;

phenoxy or phenylalkoxy having 1 to 4 carbon atoms in the alkyl moiety,each of which is optionally substituted by halogen, alkyl, alkoxy,alkylthio, alkylsulfinyl or alkylsulfonyl having 1 to 4 carbon atoms,halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl orhalogenoalkylsulfonyl having 1 to 4 carbon atoms and 1 to 9 halogenatoms,

heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylsulfinyl orheterocyclylsulfonyl having 5 or 6 ring members and being in each caseoptionally substituted by halogen, alkyl, alkoxy, alkylthio,alkylsulfinyl or alkylsulfonyl having 1 to 4 carbon atoms,halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfmyl orhalogenoalkylsulfonyl having 1 to 4 carbon atoms and 1 to 9 halogenatoms or phenyl,

or a grouping

 in which

A¹ represents hydrogen or alkyl having 1 to 4 carbon atoms or cycloalkylhaving 3 to 6 carbon atoms and

A² represents hydroxyl, amino, methylamino, methyl, phenyl, benzyl,alkoxy, alkylamino, dialkylamino having 1 to 4 carbon atoms in therespective alkyl chains and

L¹, L², L³ and L⁴ are identical or different and independently of oneanother each represents hydrogen, halogen, cyano, nitro, representsalkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in eachcase 1 to 6 carbon atoms and being in each case optionally substitutedby 1 to 5 halogen atoms, preferably represents hydrogen or methyl and inparticular hydrogen.

Particular preference is given to substituted oximes of the formula (I),in which

E represents methoxy, ethoxy, amino or methylamino,

G represents a grouping

 in which

R¹ and R² are identical or different and independently of one anotherrepresent in each case optionally fluorine-, chlorine- ormethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, acetyl, propionyl, allyl, crotonyl, propargyl or representoptionally fluorine-, chlorine-, methyl- or methoxy-substitutedcyclopentyl or cyclohexyl or represent phenyl, benzyl or benzoyl, eachof which is optionally substituted in the phenyl moiety, thesubstituents being selected from the list below:

fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,methylthio, ethylthio, n- or i-propylthio, methylsulfinyl,ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl,trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, pentafluoroethoxy,2-chloro-1,1,2-trifluoroethoxy, difluoromethylthio, trifluoromethylthio,difluorochloromethylthio, trifluoromethylsulfinyl ortrifluoromethylsulfonyl,

R¹ and R² together with the nitrogen atom to which they are attachedform a pyrrole, pyrrolidine, imidazole or triazole ring,

R represents methyl, ethyl, n- or i-propyl, or represents cyclopropyl,cyclobutyl, cyclopentyl or phenyl, each of which is optionally mono- totetrasubstituted by fluorine, chlorine, methyl or ethyl,

Z represents cyano, methoxycarbonyl, ethoxycarbonyl, methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, trifluoroethyl,methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfonyl,ethylsulfonyl, cyclopentyloxy or cyclohexyloxy or

represents cyclopentyl or cyclohexyl, each of which is optionally mono-to tetrasubstituted by fluorine, chlorine, methyl or ethyl; or

represents optionally methyl-, ethyl-, fluorine-, chlorine-, bromine-,trifluoromethyl-, phenyl-substituted thienyl, pyridyl, frryl,piperazinyl, thiazolyl, dioxazinyl, benzimidazolyl, benzothiazolyl,benzofuranyl, benzopyrazolyl, dibenzothiazinyl, thienylmethyl,pyridylmethyl or furylmethyl;

or represents benzyl 1-phenylethyl or 2-phenylethyl, each of which isoptionally mono- to tetrasubstituted by identical or differentsubstituents, represents in particular substituted phenyl, the possiblesubstituents preferably being selected from the list below:

fluorine, chlorine, bromine, cyano, nitro, amino, carbamoyl,thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,methoxymethyl, methoxy, ethoxy, n- or i-propoxy,

methylthio, ethylthio, n- or i-propylthio, methylsulfinyl,ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

methylaminomethyl, dimethylaminomethyl,

vinyl, allyl, 2-methylallyl, propen-1-yl, crotonyl, propargyl, vinyloxy,allyloxy, 2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy;

trifluoromethyl, trifluoroethyl,

difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,trifluoroethoxy, pentafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy,difluoromethylthio,

trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinylor trifluoromethylsulfonyl,

methylamino, ethylamino, n- or i-propylamino, dimethylamino,diethylamino, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl,ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl,cyclopentyl, cyclohexyl, cyclopentyloxy, cyclohexyloxy,

in each case doubly attached propanediyl, ethyleneoxy, methylenedioxy,ethylenedioxy, each of which is optionally mono- to tetrasubstituted byidentical or different substituents from the group consisting offluorine, chlorine, methyl and trifluoromethyl

in each case optionally fluorine-, chlorine-, methyl-, trifluoromethyl-or methoxy-substituted phenoxy or benzyl,

heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylsulfinyl orheterocyclylsulfonyl having 5 or 6 ring members and being in each caseoptionally substituted by halogen, alkyl, alkoxy, alkylthio,alkylsulfinyl or alkylsulfonyl having 1 to 4 carbon atoms,halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl orhalogenoalkylsulfonyl having 1 to 4 carbon atoms and 1 to 9 halogenatoms or phenyl,

represents optionally methyl-, ethyl-, fluorine-, chlorine-, bromine-,trifluoromethyl-, phenyl-substituted thienyl, imidazolyl, thiadiazolyl,pyridyl, furyl, piperazinyl, thiazolyl, dioxazinyl,thiadiazolylsulfonyl;

or a grouping

 where

A¹ represents hydrogen or methyl and

A² represents hydroxyl, methoxy, ethoxy, amino, methylamino, methyl,phenyl or benzyl, and

L¹, L², L³ and L⁴ are identical or different and independently of oneanother each represents hydrogen, fluorine, chlorine, bromine, cyano,nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy,ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl,ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl,trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroetioxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthlio, trifluoromethylsulfinylor trifluoromethylsulfonyl, preferably represents hydrogen or [lacuna]and in particular hydrogen.

Independently of the abovementioned definitions, R¹ and R² in particularrepresent methyl, ethyl, n- or i-propyl, benzyl or6-chloropyridin-3-ylmethyl, preferably methyl.

Preference is given to compounds in which L¹, L², L³ and L⁴ representhydrogen.

Preference is given to compounds in which E represent amino, methylaminoor, in particular, methoxy.

Preference is given to compounds in which R represents methyl.

Preference is given to compounds in which G represents

The abovementioned general or preferred radical definitions apply bothto the end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation.

These radical definitions can be combined with one another as desired,i.e. including combinations between the given ranges of preferredcompounds.

The formula (II) provides a general definition of the oximes required asstarting materials for carrying out the process according to theinvention. In this formula (II), G, R and Z preferably or in particularhave those meanings which have already been mentioned, in connectionwith the description of the compounds of the formula (I) according tothe invention, as being preferred or as being particularly preferred forG, R and Z.

The oximes of the formula (II) are known or can be prepared by knownmethods (compare, for example, WO 96-32373 and WO 97-06133).

The formula (III) provides a general definition of the halogen compoundsfurther required as starting materials for carrying out the processaccording to the invention. In this formula (III), E, L¹, L², L³ and L⁴preferably or in particular have those meanings which have already beenmentioned in connection with the description of the compounds of theformula (I) according to the invention as being preferred or as beingparticularly preferred for E, L¹, L², L³ and L⁴. X represents halogen,preferably chlorine or bromine.

The halogen compounds of the formula (III) are known and can be preparedby known methods (compare EP-A 525516).

Suitable diluents for carrying out the process according to theinvention are all inert organic solvents. These preferably includealiphatic, alicyclic or aromatic hydrocarbons, such as, for example,petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane,benzene, toluene, xylene or decaline; halogenated hydrocarbons, such as,for example, chlorobenzene, dichlorobenzene, dichloromethane,chloroform, carbon tetrachloride, dichloroethane or trichloroethane;ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether,methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,1,2-diethoxyethane or anisole; sulfoxides, such as dimethyl sulfoxide;or sulfones, such as sulfolane.

The process according to the invention is, if appropriate, carried outin the presence of a suitable acid acceptor. Suitable acid acceptors areall customary inorganic or organic bases. These preferably includealkaline earth metal or alkali metal hydrides, hydroxides, amides,alkoxides, carbonates or bicarbonates, such as, for example, sodiumhydride, sodium amide, sodium methoxide, sodium ethoxide, potassiumtert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate,potassium carbonate, potassium bicarbonate or sodium bicarbonate, andalso tertiary amines, such as trimethylamine, triethylamine,tributylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine,N-methylpiperidine, N-methylmoipholine, N,N-dimethylaminopyridine,diazabicyclooctane (DABCO), diazabicyclononene (DBN) ordiazabicycloundecene (DBU).

When carrying out the process according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the process is carried out at temperatures from 20° C. to 180° C.,preferably at temperatures from 20° C. to 150° C.

For carrying out the process according to the invention for preparingthe compounds of the formula (a), in general from 0.5 to 2 mol,preferably from 0.8 to 1.5 mol. of halogen compound of the formula (III)are employed per mole of oxime of the formula (II).

The process according to the invention is generally carried out underatmospheric pressure. However, it is also possible to operate underelevated or reduced pressure—in general between 0.1 bar and 10 bar.

The practice of the reaction and the work-up and isolation of thereaction products are carried out by generally customary processes(compare also the Preparation Examples).

The compounds according to the invention have potent microbicidalactivity and can be employed for controlling undesirable microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicides are employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides are employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above are mentioned as examples, but not by wayof limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Bremia species, such as, for example, Bremia lactucae;

Peronospora species, such as, for example, Peronospora pisi or P.brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P.graminea (conidia form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus(conidia form: Drechslera, syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Altemaria species, such as, for example, Alternaria brassicae; and

Pseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of aerial parts of plants, of propagation stock and seeds, andof the soil.

The active compounds according to the invention can be employedparticularly successfully for controlling cereal diseases such as, forexample, against Erysiphe species and Leptosphaeria species.

The active compounds according to the invention are also suitable forincreasing the harvest yield. Moreover, they have reduced toxicity andare tolerated well by plants.

In the protection of materials, the compounds according to the inventioncan be employed for protecting industrial materials against infectionwith, and destruction by, undesired microorganisms.

Industrial materials in the present context are understood as meaningnon-living materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be adhesives, sizes, paper and board, textiles, leather,wood, paints and plastic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the proliferation of microorganisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably adhesives, sizes, paper and boards, leather,wood, paints, cooling lubricants and heat-transfer liquids, particularlypreferably wood.

Microorganisms capable of degrading or changing the industrial materialswhich may be mentioned are, for example, bacteria, fungi, yeasts, algaeand slime organisms. The active compounds according to the inventionpreferably act against fungi, in particular molds, wood-discoloring andwood-destroying fungi (Basidiomycetes) and against slime organisms andalgae.

Microorganisms of the following genera may be mentioned as examples:

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, such as Chaetomium globosum,

Coniophora, such as Coniophora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus versicolor,

Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride,

Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa,

Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted to the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to employ,for example, organic solvents as auxiliary solvents. Suitable liquidsolvents are essentially: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, alcohols such as butanol or glycol andtheir ethers and esters, ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide and dimethyl sulfoxide, or else water. Liquefiedgaseous extenders or carriers are to be understood as meaning liquidswhich are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as highlydisperse silica, alumina and silicates. Suitable solid carriers forgranules are: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, or else syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks.Suitable emulsifiers and/or foam formers are: for example nonionic andanionic emulsifiers, such as polyoxyethylene fatty acid esters,polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycolethers, alkylsulfonates, alkyl sulfates, arylsulfonates, or else proteinhydrolysates. Suitable dispersants are: for example ligno-sulfite wasteliquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecitgins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such orin their formulations also mixed with known fungicides, bactericides,acaricides, nematicides or insecticides in order thus, for example, towiden the spectrum of action or to prevent development of resistance. Inmany cases, synergistic effects are achieved, i.e. the activity of themixture exceeds the activity of the individual components.

Examples of co-components in mixtures are the following compounds:

Fungicides:

aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulfide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamine, dipyfithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminum, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulfate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxamn, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB),

sulfur and sulfur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclasis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamide, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-fluoro-b-propyl-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,

α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

(E)-a-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

1-isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanoneO-(phenylmethyl)-oxime,

1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,

1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,

1-[(diiodomethyl)-sulfonyl]-4-methyl-benzene,

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol,

2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,

2,6-dichloro-5-(methylthio)-4-pyrimidinyl thiocyanate,

2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

2-[(1-methylethyl)sulfonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-a-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

2-aminobutane,

2-bromo-2-(bromomethyl)-pentanedinitrile,

2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

2-phenylphenol (OPP),

3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,

3,5-dichloro-N-[cyano-[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,

3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide,

4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

8-hydroxyquinoline sulfate,

9H-xanthene-9-carboxylic-[(phenylamino)-carbonyl]hydrazide,

bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,

cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,

ethyl [(4-chlorophenyl)-azo]-cyanoacetate,

potassium hydrogencarbonate,

methanetetrathiol sodium salt,

methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulfonamide,

N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetaride,

N-(6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,

N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,

N-formyl-N-hydroxy-DL-alanine-sodium salt,

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

O-methyl S-phenyl phenylpropylphosphoramidothioate,

S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

spiro[2H]-1-benzopyran-2,1′(3′H)-isobenzofuran]-3′-one,

Bactericides:

bromopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline,probenazole, streptomycin, tecloftalam, copper sulfate and other copperpreparations.

Insecticides/Acaricides/Nematicides:

abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz, avernectin, AZ60541, azadirachtin, aza-methiphos, azinphos A, azinphos M, azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillusthuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,bifenazate, bifenthrin, bioethanomethrin, biopermethrin, BPMC, bromophosA, bufencarb, buprofezin, butathiofos, butocarboxim, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, cis-resmethrin, cispermethrin, clocythrin, cloethocarb,clofentezine, cyanophos, cycloprene, cycloprothrin, cyfluthrin,cyhalothrin, cyhexatin, cypermethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlorvos, diflubenzuron, dimethoate, dimethylvinphos,diofenolan, disulfoton, docusat-sodium, dofenapyn,

efusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp.,esfenvalerate, ethiofencarb, ethion, ethoprophos, etofqnprox, etoxazole,etrimfos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb,fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin,fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron,flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox,filrathiocarb,

granulosis viruses

halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene,

imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,

nuclear polyhedrosis viruses

lambda-cyhalothrin, lufenuron

malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, monocrotophos,

naled, nitenpyram, nithiazine, novaluron

omethoate, oxamyl, oxydemethon M

Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb, propoxur,prothiofos, prothoate, pymetrozine, pyraclofos, pyresmethrin, pyrethrum,pyridaben, pyridathion, pyrimidifen, pyriproxyfen,

quinalphos,

ribavirin

salithion, sebufos, silafluofen, spinosad, sulfotep, sulprofos,

tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, theta-cypermethrin, thiamethoxam, thiapronil,thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox,thuringiensin, tralocythrin, tralomethrin, triarathene, triazamate,triazophos, triazuron, trichlophenidine, trichlorfon, triflumuron,trimethacarb,

vamidothion, vaniliprole, Verticillium lecanii

YI 5302

zeta-cypermethrin, zolaprofos

(1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,

(3-phenoxyphenyl)-methyl 2,2,3,3-tetramethylcyclopropanecarboxylate,

1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine

2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,

2-(acetlyoxy)-3-dodecyl-1,4-naphthalenedione

2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide

2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,

3-methylphenyl propylcarbamate,

4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,

4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,

4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

Bacillus thuringiensis strain EG-2348,

2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,

2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-ylbutanoate,

[3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,

dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,

ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,

N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,

N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,

N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,

N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate.

It is also possible to admix other known active compounds, such asherbicides, or fertilizers and growth regulators.

The active compounds can be used as such or in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. They are used in the customary manner, for example bypouring, spraying, atomizing, spreading, dusting, foaming, brushing onand the like. It is further possible to apply the active compounds bythe ultra-low volume method or to inject the active compoundformulation, or the active compound itself, into the soil. The seed ofthe plants can also be treated.

When using the active compounds according to the invention asfungicides, the application rates can be varied within a relatively widerange, depending on the type of application. In the treatment of partsof plants, the application rates of active compounds are generallybetween 0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. In thetreatment of seed, the application rates of active compounds aregenerally between 0.001 and 50 g per kilogram of seed, preferablybetween 0.01 and 10 g per kilogram of seed. In the treatment of thesoil, the application rates of active compound are generally between 0.1and 10, 000 g/ha, preferably between 1 and 5000 g/ha.

The compositions used for protecting industrial materials comprise theactive compounds generally in an amount of from 1 to 95%, preferablyfrom 10 to 75%.

The use concentrations of the active compounds according to theinvention depend on the species and the occurrence of the microorganismsto be controlled, and on the composition of the material to beprotected. The optimum rate of application can be determined by testseries. The use concentrations are generally in the range from 0.001 to5% by weight, preferably from 0.05 to 1.0% by weight, based on thematerial to be protected.

The activity and the activity spectrum of the active compounds to beused according to the invention in the protection of materials, or thecompositions, concentrates or quite generally formulations preparabletherefrom, can be increased by adding, if appropriate, otherantimicrobially active compounds, fungicides, bactericides, herbicides,insecticides or other active compounds for broadening the activityspectrum or obtaining particular effects, such as, for example, theadditional protection against insects. These mixtures may have a broaderactivity spectrum than the compounds according to the invention.

PREPARATION EXAMPLES Example (1)

A solution of 1.63 g (10 mMol) of methyl2-hydroxyamino-N-methoxy-thiopropionimidate in 80 ml ofdimethylformamide is cooled to 0° C., admixed with 333 mg (10 mMol) ofsodium hydride (75% strength) and stirred without further cooling for 2hours. 2.85 g (10 mMol) of methyl3-(2-bromomethyl-phenyl)-3-methoxy-acrylate are then added, and themixture is stirred at 20° C. for 18 hours. The reaction mixture ispoured into water and extracted twice with ethyl acetate. The combinedorganic phases are washed with saturated sodium chloride solution, driedover sodium sulfate and concentrated under reduced pressure. The residueis chromatographed over silica gel using cyclohexane/ethyl acetate(4:1).

This gives 3.07 g (84% of theory) of methyl3-methoxy-3-[2-(2-methoxyamino-1-methyl-2-methylthio-ethylideneaminooxymethyl)-phenyl]-acrylate.

HPLC: logP=3.5

Example (2)

340 mg (0.93 mMol) of methyl3-methoxy-3-[2-(2-methoxyimino-1-methyl-2-methylthioethylideneaminooxymethyl)-phenyl]-acrylateare dissolved in a mixture of 2 ml of carbon tetrachloride, 2 ml ofacetonitrile and 4 ml of water, and the mixture is cooled to 10° C. 640mg (3.0 mMol) of sodium periodate and 1 mg (0.005 mMol) of ruthenium-IIIchloride hydrate are added, and the mixture is stirred at 20° C. for 3hours. The reaction mixture is poured into water and extracted threetimes with ethyl acetate. The combined organic phases are washed withsodium chloride solution, dried over sodium sulfate and concentratedunder reduced pressure. The residue is chromatographed over silica gelusing cyclohexane/ethyl acetate (1:1). This gives 320 mg (86% of theory)of methyl3-[2-(2-methanesulfonyl-2-methoxyimino-1-methyl-ethylideneaminooxymethyl)-phenyl]-3-methoxy-acrylate.

HPLC: logP=2.79

Example (3)

0.21 ml (1.0 mMol) of a 30% strength sodium methoxide solution inmethanol are added to a solution of 200 mg (0.5 mMol) of methyl3-[2-(2-methanesulfonyl-2-methoxyimino-1-methyl-ethylideneaminooxymethyl)-phenyl]-3-methoxy-acrylatein 10 ml of tetrahydrofuran, and the mixture is stirred at 20° C. for 4hours. The reaction mixture is poured into a saturated ammonium chloridesolution and extracted three times with ethyl acetate. The combinedorganic phases are dried over sodium sulfate and concentrated underreduced pressure. The residue is chromatographed over silica gel usingcyclohexane/ethyl acetate (1:1).

This gives 160 mg (91% of theory) of methyl3-methoxy-3-[2-(2-methoxy-2-methoxyimino-1-methyl-ethylideneaminooxymethyl)-phenyl]-acrylate.

HPLC: logP=3.05

Analogously to Examples (1-3), and in accordance with the generaldescription of the preparation process according to the invention, it isalso possible to obtain the compounds of the formula (I-a) according tothe invention listed in Table 1 below:

TABLE 1 Ex. No. G Z E Phys. data 4

phenyl —OCH₃ logP(s): 4.2 5

—CH₃ —OCH₃ 6

—CH₃ —OCH₃ logP(n): 3.9 7

-i-C₃H₇ —OCH₃ logP(n): 4.6 8

—COOCH₃ —OCH₃ logP(s): 3.3 9

-i-C₃H₇ —OCH₃ logP(s): 5.2 10

-i-C₃H₇ —OCH₃ logP(s): 5.6 11

-i-C₃H₇ —OCH₃ logP(s): 5.52 12

-i-C₃H₇ —OCH₃ log(s): 5.23 13

-O-i-C₃H₇ —OCH₃ logP(s): 3.73 14

-i-C₃H₇ —NHCH₃ logP(s): 3.91 15

-i-C₃H₇ —NH₂ logP(s): 3.57 16

—OC₂H₅ —OCH₃ logP(s): 3.40 17

—OC₂H₅ —OC₂H₅ logP(s): 3.75

The ¹H-NMR spectra were recorded in deuterochloroform (CDCl₃) orhexa-deuterodimethyl sulfoxide (DMSO-d₆) using tetramethylsilane (TMS)as internal standard. What is stated is the chemical shift as δ value inppm.

The logP values were determined in accordance with EEC Directive 79/831Annex V. A8 by HPLC (gradient method, acetonitrile/0.1% aqueousphosphoric acid (s) or gradient method, acetonitrile/0.1% water (n))

USE EXAMPLES Example A

Leptosphaeria nodorum test (wheat)/protective

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are sprayed with a sporesuspension of Leptosphaeria nodorum. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours.

The plants are placed in a greenhouse at a temperature of about 15° C.and a relative atmospheric humidity of 80%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the compound according to the invention listed in Example(4) exhibits, at an application rate of 250 g/ha, an efficacy of 90% ormore.

Example B

Erysiphe test (barley)/protective

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

After the spray coating has dried on, the plants are dusted with sporesof Erysiphe graminis f.sp. hordei.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidity of about 80% to promote thedevelopment of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the compound according to the invention listed in Example(4) exhibits, at an application rate of 250 g/ha, an efficacy of 90% ormore.

Example C

Erysiphe test (wheat)/protective

Solvent: 25 parts by weight of N,N-dimethylacetarnide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

After the spray coating has dried on, the plants are dusted with sporesof Erysiphe graminis f.sp. hordei.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidity of about 80% to promote thedevelopment of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the compounds according to the invention listed inExamples (6) and (7) exhibit, at an application rate of 250 g/ha, anefficacy of 100%.

Example D

Erysiphe test (wheat)/curative

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for curative activity, young plants are dusted with spores ofErysiphe graminis f.sp. tritici. 48 hours after the inoculation, theplants are sprayed with the preparation of active compound at the statedapplication rate.

The plants are placed in a greenhouse at a temperature of 20° C. and arelative atmospheric humidity of about 80% to promote the development ofmildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention listed inExamples (6) and (7) exhibit, at an application rate of 250 g/ha, anefficacy of 100%.

Example E

Puccinia test (wheat)/protective

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are sprayed with a conidiasuspension of Puccinia recondita. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours.

The plants are then placed in a greenhouse at a temperature of about 20°C. and a relative atmospheric humidity of about 80% to promote thedevelopment of mildew pustules.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the compound according to the invention listed in Example(7) exhibits, at an application rate of 250 g/ha, an efficacy of 100%.

Example F

Erysiphe test (barley)/curative

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are dusted with spores ofErysiphe graminis f.sp. hordei. 48 hours after the inoculation, theplants are sprayed with the preparation of active compound at the statedapplication rate.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidity of about 80% to promote thedevelopment of mildew pustules.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the compound according to the invention listed in Example(7) exhibits, at an application rate of 250 g/ha, an efficacy of 100%.

Example G

Plasmopara test (grapevine)/protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Plasmopara viticola and then remain in an incubationcabin at about 20° C. and 100% relative atmospheric humidity for 1 day.The plants are then placed in a greenhouse at about 21° C. and about 90%atmospheric humidity for 5 days. The plants are then moistened andplaced in an incubation cabin for 1 day.

Evaluation is carried out 6 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the compound according to the invention listed in Example(4) exhibits, at an application rate of 100 g/ha, an efficacy of 90% ormore.

Example H

Venturia test (apple)/protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration. To test for protective activity, young plants are sprayedwith the preparation of active compound at the stated application rate.After the spray coating has dried on, the plants are inoculated with anaqueous conidia suspension of the causative organism of apple scabVenturia inaequalis and then remain in an incubation cabin at about 20°C. and 100% relative atmospheric humidity for 1 day.

The plants are then placed in a greenhouse at about 21° C. and arelative atmospheric humidity of about 90%.

Evaluation is carried out 12 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the compound according to the invention listed in Example(4) exhibits, at an application rate of 10 g/ha, an efficacy of 100%.

Example I

Pyricularia test (rice)/protective

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young rice plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Pyricularis oryzae and then remain at 100% rel.atmospheric humidity and 26° C. for 24 h. The plants are then placed ina greenhouse at 80% rel. atmospheric humidity and 26° C.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the compound according to the invention listed in Example(7) exhibits, at an application rate of 125 g/ha, an efficacy of 97% ormore.

What is claimed is:
 1. A compound of the formula (I),

wherein E represents methoxy, ethoxy, amino or methylamino, G representsa grouping

 wherein R¹ and R² are identical or different and independently of oneanother each represents unsubstituted or substituted alkyl, alkenyl,alkinyl, aryl, cycloalkyl, alkylcarbonyl or arylcarbonyl, or R¹ and R²together with the nitrogen atom to which they are attached form asaturated or unsaturated heterocyclic ring, and Z represents cyano,alkoxycarbonyl, alkoxy, alkylthio, alkylsulfonyl, cycloalkoxy or in eachcase unsubstituted or substituted alkyl, cycloalkyl, cycloalkylalkyl,aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, R representshydrogen, alkyl or in each case unsubstituted or substituted cycloalkylor aryl, and L¹, L², L³ and L⁴ are identical or different andindependently of one another each represents hydrogen, halogen, cyano,nitro, in each case unsubstituted or halogen-substituted alkyl, alkoxy,alkylthio, alkylsulfinyl or alkylsulfonyl.
 2. A compound according toclaim 1, wherein E represents methoxy, ethoxy, amino or methylamino, Grepresents a grouping

 wherein R¹ and R² are identical or different and independently of oneanother each represents alkyl or alkylcarbonyl having 1 to 6 carbonatoms, alkenyl having 2 to 6 carbon atoms or alkinyl having 2 to 6carbon atoms, each of which is unsubstituted or substituted by halogenor alkoxy having 1 to 4 carbon atoms, or represents cycloalkyl having 3to 8 carbon atoms, which is unsubstituted or substituted by halogen,alkyl or alkoxy having in each case 1 to 4 carbon atoms, or representsphenyl, phenylalkyl or heterocyclylalkyl having 1 to 4 carbon atoms inthe alkyl moiety or phenylcarbonyl, each of which is unsubstituted orsubstituted in the phenyl moiety or heterocyclyl moiety, thesubstituents being selected from the list below: halogen, cyano, nitro,alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in eachcase 1 to 6 carbon atoms, halogenoalkyl, halogenoalkoxy,halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl havingin each case 1 to 6 carbon atoms and 1 to 13 identical or differenthalogen atoms, in each case halogenoalkenyl or halogenoalkenyloxy havingin each case 2 to 6 carbon atoms and 1 to 11 identical or differenthalogen atoms, or R¹ and R² together with the nitrogen atom to whichthey are attached form a saturated or unsaturated heterocyclic ringhaving 5 or 6 ring members, R represents alkyl having 1 to 4 carbonatoms or represents cycloalkyl having 3 to 6 carbon atoms or phenyl,each of which is unsubstituted or mono- to tetrasubstituted by halogenor alkyl, Z represents cyano, alkoxycarbonyl, alkoxy, alkylthio oralkylsulfonyl having in each case 1 to 4 carbon atoms in the alkylmoiety, cycloalkoxy having 5 or 6 carbon atoms; or represents alkyl orhalogenoalkyl having in each case 1 to 4 carbon atoms and being in eachcase unsubstituted or monosubstituted by cyano or alkoxy, or representscycloalkyl or cycloalkylalkyl having in each case 3 to 7 carbon atoms inthe cycloalkyl moiety and 1 to 4 carbon atoms in the alkyl moiety, eachof which is unsubstituted or mono- to tetrasubstituted by halogen oralkyl; or represents heterocyclyl, benzoheterocyclyl,dibenzoheterocyclyl or heterocyclylalkyl having in each case 3 to 7 ringmembers in the heterocyclyl moiety and 1 to 4 carbon atoms in the alkylmoiety and being unsubstituted or substituted by halogen, alkyl, alkoxy,alkylthio, alkylsulfinyl or alkylsulfonyl having 1 to 4 carbon atoms,halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl orhalogenoalkylsulfonyl having 1 to 4 carbon atoms and 1 to 9 halogenatoms or phenyl: or represents aryl or arylalkyl having in each case 6to 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in thealkyl moiety and being in each case unsubstituted or mono- totetrasubstituted in the aryl moiety by identical or differentsubstituents, the possible substituents being selected from the listbelow: halogen, cyano, nitro, amino, carbamoyl, thiocarbamoyl; in eachcase straight-chain or branched alkyl, alkoxy, alkoxyalkyl,alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylthio,alkylsulfinyl or alkylsulfonyl having in each case 1 to 8 carbon atoms;in each case straight-chain or branched alkenyl or alkenyloxy having ineach case 2 to 6 carbon atoms; in each case straight-chain or branchedhalogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinylor halogenoalkylsulfonyl having in each case 1 to 6 carbon atoms and 1to 13 identical or different halogen atoms; in each case straight-chainor branched halogenoalkenyl or halogenoalkenyloxy having in each case 2to 6 carbon atoms and 1 to 11 identical or different halogen atoms; ineach case straight-chain or branched alkylamino, dialkylamino,alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl orarylalkylaminocarbonyl having 1 to 6 carbon atoms in the respectivehydrocarbon chains; cycloalkyl or cycloalkyloxy having in each case 3 to6 carbon atoms; in each case doubly attached alkylene having 3 or 4carbon atoms, oxyalkylene having 2 or 3 carbon atoms or dioxyalkylenehaving 1 or 2 carbon atoms, each of which is unsubstituted or mono- totetrasubstituted by identical or different substituents from the groupconsisting of fluorine, chlorine, methyl trifluoromethyl and ethyl;phenoxy or phenylalkoxy having 1 to 4 carbon atoms in the alkyl moiety,each of which is unsubstituted or- substituted by halogen, alkyl,alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having 1 to 4 carbonatoms, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl orhalogenoalkylsulfonyl having 1 to 4 carbon atoms and 1 to 9 halogenatoms, heterocyclyl, heterocyclyloxy, heterocyclylthio,heterocyclylsulfinyl or heterocyclylsulfonyl having 5 or 6 ring membersand being in each case unsubstituted or substituted by halogen, alkyl,alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having 1 to 4 carbonatoms, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl orhalogenoalkylsulfonyl having 1 to 4 carbon atoms and 1 to 9 halogenatoms or phonyl, or a grouping

 wherein A¹ represents hydrogen or alkyl having 1 to 4 carbon atoms orcycloalkyl having 3 to 6 carbon atoms and A² represents hydroxyl, amino,methylamino, methyl, phenyl, benzyl, alkoxy, alkylamino, dialkylaminohaving 1 to 4 carbon atoms in the respective alkyl chains and L¹, L², L³and L⁴ are identical or different and independently of one another eachrepresents hydrogen, halogen, cyano, nitro, or represents alkyl, alkoxy,alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 6carbon atoms and being in each case unsubstituted or substituted by 1 to5 halogen atoms.
 3. A compound according to claim 1, wherein Erepresents methoxy, ethoxy, amino or methylamino, G represents agrouping

 wherein R¹ and R² are identical or different and independently of oneanother represent in each case unsubstituted or fluorine-, chlorine- ormethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, acetyl, propionyl, allyl, crotonyl, propargyl or representunsubstituted or fluorine-, chlorine-, methyl- or methoxy-substitutedcyclopentyl or cyclohexyl or represent phenyl, benzyl or benzoyl, eachof which is unsubstituted or substituted in the phenyl moiety, thesubstituents being selected from the list below: fluorine, chlorine,bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl orethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy,trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy,pentafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, difluoromethylthio,trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinylor trifluoromethylsulfonyl, R¹ and R² together with the nitrogen atom towhich they are attached form a pyrrole, pyrrolidine, imidazole ortriazole ring, R represents methyl, ethyl, n- or i-propyl, or representscyclopropyl, cyclobutyl, cyclopentyl or phenyl, each of which isunsubstituted or mono- to tetrasubstituted by fluorine, chlorine, methylor ethyl, Z represents cyano, methoxycarbonyl, ethoxycarbonyl, methyl,ethyl, n-or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl,trifluoroethyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio,methylsulfonyl, ethylsulfonyl, cyclopentyloxy or cyclohexyloxy, orrepresents cyclopentyl or cyclohexyl, each of which is unsubstituted ormono- to tetrasubstituted by fluorine, chlorine, methyl or ethyl; orrepresents unsubstituted or methyl-, ethyl-, fluorine-, chlorine-,bromine-, trifluoromethyl-, phenyl-substituted thienyl, pyridyl, furyl,piperazinyl, thiazolyl, dioxazinyl, benzimidazolyl, benzothiazolyl,benzofuranyl, benzopyrazolyl, dibenzothiazinyl, thienylmethyl,pyridylmethyl or furylmethyl; or represents benzyl, 1-phenylethyl or2-phenylethyl, each of which is unsubstituted or mono- totetrasubstituted by identical or different substituents, or substitutedphenyl, the possible substituents being selected from the list below:fluorine, chlorine, bromine, cyano, nitro, amino, carbamoyl,thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,methoxymethyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio,n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl orethylsulfonyl, methylaminomethyl, dimethylaminomethyl, vinyl, allyl,2-methylallyl, propen-1-yl, crotonyl, propargyl, vinyloxy, allyloxy,2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy;trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, pentafluoroethoxy,2-chloro-1,1,2-trifluoroethoxy, difluoromethylthio, trifluoromethylthio,difluorochloromethylthio, trifluoromethylsulfinyl ortrifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino,dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl,methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl,diethylaminocarbonyl, cyclopentyl, cyclohexyl, cyclopentyloxy,cyclohexyloxy, in each case doubly attached propanediyl, ethyleneoxy,methylenedioxy, ethylenedioxy, each of which is unsubstituted or mono-to tetrasubstituted by identical or different substituents from thegroup consisting of fluorine, chlorine, methyl and trifluoromethyl ineach case unsubstituted or fluorine-, chlorine-, methyl-,trifluoromethyl- or methoxy-substituted phenomy or benzyl, heterocyclyl,heterocyclyloxy, heterocyclylthio, heterocyclylsulfinyl orheterocyclylsulfonyl having 5 or 6 ring members and being in each caseunsubstituted or substituted by halogen, alkyl, alkoxy, alkylthio,alkylsulfinyl or alkylsulfonyl having 1 to 4 carbon atoms,halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl orhalogenoalkylsulfonyl having 1 to 4 carbon atoms and 1 to 0 halogenatoms or phenyl, or represents unsubstituted methyl-, ethyl-, fluorine-,chlorine-, bromine-, trifluoromethyl-, phenyl-substituted thienyl,imidazolyl, thiadiazolyl, pyridyl, furyl, piperazinyl, thiazolyi,dioxazinyl, thiadiazolylsulfonyl; or a grouping

 where A¹ represents hydrogen or methyl and A² represents hydroxyl,methoxy, ethoxy, amino, methylamino, methyl, phenyl or benzyl, and L¹,L², L³ and L⁴ are identical or different and independently of oneanother each represents hydrogen, fluorine, chlorine, bromine, cyano,nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy,ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl,ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl,trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinylor trifluoromethylsulfonyl.
 4. A compound according to claim 1, whereinR¹ and R² represent methyl, ethyl, n- or i-propyl, benzyl or6-chloropyridin-3-ylmethyl.
 5. A composition comprising a compoundaccording the claim 1 and extenders and/or carriers.
 6. A process forpreparing compositions, comprising the step of mixing a compoundaccording to claim 1 with extenders and/or carriers and/or surfactants.7. A process for preparing a compound according to claim 1, comprisingthe step of reacting an oxime of the formula (II)

wherein G, R and Z are as defined in claim 1 with a halogen compound ofthe formula (III)

wherein E, L¹, L², L³ and L⁴ are as defined in claim 1 and X representshalogen.
 8. A compound according to claim 2, wherein G represents


9. A compound according to claim 2, wherein L¹, L², L³ and L⁴ eachindependently represent hydrogen or methyl.
 10. A compound according toclaim 9, wherein L¹, L², L³ and L⁴ each represent hydrogen.
 11. Acompound according to claim 2, wherein R represents methyl orcylcopropyl.
 12. A compound according to claim 11, wherein R representsmethyl.
 13. A compound according to claim 2, wherein E representsmethoxy.
 14. A compound according to claim 2, wherein E represents aminoor methylamino.
 15. A method of control microorganisms, comprising thestep of applying a compound according to claim 1 to microorganismsand/or their habitat.
 16. A method of control microorganisms, comprisingthe step of applying a composition according to claim 5 tomicroorganisms and/or their habitat.